Festivals in Winter Park

Check out happening festivals events all around Winter Park, FL

The 67th Winter Park Sidewalk Art Festival

 Fri, 20 Mar at 09:00 am Park Avenue, Winter Park

Taste of Winter Park

 Wed, 01 Apr at 06:30 pm Winter Park Farmers' Market Venue USD 55 to 384

1st Annual Holler Ford Racing Showcase

 Sat, 14 Mar at 05:00 pm 1875 South Orlando Avenue, Maitland, FL, United States, Florida 32751

Smile Mile - Kids Run

 Sat, 14 Mar at 08:00 am Blue Jacket Park

The Great Duck Derby

 Sat, 28 Mar at 10:00 am Mead Botanical Garden Free

Winter Park Sidewalk Art Festival Celebration

 Fri, 20 Mar at 09:30 am 445 N Park Ave, Winter Park, FL, United States, Florida 32789

Las Locas Comedy Florida Tour - Aloma Cinema Grill - Winter Park - 03/13/26

 Fri, 13 Mar at 06:30 pm Aloma Cinema Grill

Silver Screen Classics

 Sat, 25 Apr at 07:30 pm Knowles Memorial Chapel

Sacred Service Duke Ellington with Samuel McKelton

 Fri, 10 Apr at 07:30 pm Knowles Memorial Chapel

Silver Screen Classics

 Sun, 26 Apr at 03:00 pm Knowles Memorial Chapel

Lysander Piano Trio

 Sun, 15 Mar at 03:00 pm Tiedtke Concert Hall | 1000 Holt Ave, Winter Park, FL 32789-4499, United States

Free: Jazz Festival—Live with The Yo Cats

 Thu, 26 Mar at 07:00 pm Winter Park Events Center Free

Live Painting at George's Cafe in Winter Park

 Sat, 21 Mar at 10:00 am George's Cafe in Winter Park

25th Annual Orange Blossom Jubilee "Under the Big Top"

 Fri, 17 Apr at 06:00 pm Winter Park Events Center

Romancing the Books Festival 2026 | Keynote: Meryl Wilsner

 Sat, 28 Mar at 12:00 pm Winter Park Library Free

The Community Market

 Sun, 17 May at 01:00 pm Agape Hall Free

Arankai at Conduit

 Wed, 20 May at 07:00 pm Conduit

Auditions: A Midsummer Night's Dream by William Shakespeare

 Sat, 28 Mar at 10:00 am 6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792